Simon metabolites of alpha-tocopherol are not formed via a rate-controlling scission of the 3'C-H bond.
The major in vivo oxidation products of alpha-tocopherol, alpha-T, are the Simon metabolites, 1 and 2. For these compounds to be formed from alpha-T the polyisoprenoid tail of alpha-T must be oxidatively cleaved at the 3' carbon atom. Comparison of the levels of 2R,4'R,8'R-alpha-(3',3'-2H2)-T and 2R,4'R,8'R-alpha-[5,7-(C2H3)2]-T remaining in various tissues of rats which had been preloaded with equal quantities of these two forms of vitamin E following a change to a vitamin E-free diet has shown that there is no statistically significant difference in the rates of loss of these two deuterium-labeled alpha-T's. This demonstrates that the Simon metabolites are not formed by a rate-controlling scission of the 3'C-H bond of alpha-T.
Dutton
P J
PJ
Steacie Institute for Molecular Sciences, National Research Council of Canada, Ottawa, Ontario.
Hughes
L A
LA
Foster
D O
DO
Burton
G W
GW
Ingold
K U
KU
D000818:Animals; D005609:Free Radicals; D007700:Kinetics; D008297:Male; D010084:Oxidation-Reduction; D051381:Rats; D011919:Rats, Inbred Strains; D014810:Vitamin E / Q000737:chemistry / Q000378:metabolism*
D005609:Free Radicals; D014810:Vitamin E